The specific aim of this project is the development of practical total syntheses for the iridoid monoterpenes sarracenin and xylomollin. The laboratory routes to these naturally occurring compounds will be used to prepare quantities of radiochemically labeled material in order to examine the possibility that these terpenes are bioxynthetic precursors of the indole alkaloids. Additional materials will be prepared to examine the possibility that a hydrated form of sarracenin is the active constituent of the golden trumpet (sarracenin flavia) that is responsible for the observed TC 150 against P-388 leukemia (at 50 mg/kg) of the crude extract. This postulate is now especially intriguing in light of the demonstrated ability of the structurally quite similar terpene xylomollin to decouple respiration in rat liver mitochondria.